Tetrahedraphene: A Csp3-centered 3D molecular nanographene showing aggregation-induced emission
The bottom-up synthesis of 3D tetrakis(hexa-peri-hexabenzocoronenyl)methane, “tetrahedraphene”, isreported. This molecular nanographene constituted by four hexa-peri-hexabenzocoronene (HBC) units attached to acentral sp3 carbon atom, shows a highly symmetric arrangement of the HBC units disposed in...
| Autores: | , , , , , |
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| Formato: | artículo |
| Fecha de publicación: | 2023 |
| País: | España |
| Recursos: | Universidad Autónoma de Madrid |
| Repositorio: | Biblos-e Archivo. Repositorio Institucional de la UAM |
| Idioma: | inglés |
| OAI Identifier: | oai:repositorio.uam.es:10486/734380 |
| Acesso em linha: | https://hdl.handle.net/10486/734380 https://dx.doi.org/10.1002/anie.202312314 |
| Access Level: | acceso abierto |
| Palavra-chave: | 3D Nanographene Aggregation-Induced Emission Bottom-up Synthesis Molecular Nanographene X-Ray Diffraction Química |
| Resumo: | The bottom-up synthesis of 3D tetrakis(hexa-peri-hexabenzocoronenyl)methane, “tetrahedraphene”, isreported. This molecular nanographene constituted by four hexa-peri-hexabenzocoronene (HBC) units attached to acentral sp3 carbon atom, shows a highly symmetric arrangement of the HBC units disposed in the apex of a tetrahedron.The X-ray crystal structure reveals a tetrahedral symmetry of the molecule and the packing in the crystal is achievedmostly by CH···π interactions since the interstitial solvent molecules prevent the π···π interactions. In solution,tetrahedraphene shows the same electrochemical and photophysical properties as the hexa-tBu-substituted HBC (tBu-HBC) molecule. However, upon water addition, it undergoes a fluorescence change in solution and in the precipitatedsolid, showing an aggregation induced emission (AIE) process, probably derived from the restriction in the rotation and/or vibration of the HBCs. Time-Dependent Density Functional Theory (TDDFT) calculations reveal that uponaggregation, the high energy region of the emission band decreases in intensity, whereas the intensity of the red edgeemission signal increases and presents a smoother decay, compared to the non-aggregated molecule. All in all, theexcellent correlation between our simulations and the experimental findings allows explaining the colour changeobserved in the different solutions upon increasing the water fraction |
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